Imidazole → 1-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-one

HRID 1061637Notes

Reaction equation

HRID 1061637 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:6]=1[Cl:12])=[O:4].[NH:13]1[CH:17]=[CH:16][N:15]=[CH:14]1.ClCCl.O>C(#N)C>[Cl:12][C:6]1[CH:7]=[C:8]([Cl:11])[CH:9]=[CH:10][C:5]=1[C:3](=[O:4])[CH2:2][N:13]1[CH:17]=[CH:16][N:15]=[CH:14]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 6344DichloromethaneHCID 202502,2',4'-Trichloroacetophenone

Product 1

HCID 322321-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-yl)ethan-1-oneYield 74.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Trichlorinated derivative, 2-chloro-1-(2,4-dichlorophenyl)-ethanone (5.58 g), is added to 5.10 g of imidazole (75 mmole) in 25 ml of acetonitrile, and the reaction medium is stirred at ambient temperature for 24 hours. Then 50 ml of dichloromethane and 50 ml of water are added, followed by extracting, decanting, washing then re-extracting with dichloromethane. The organic phases are dried and evaporated under reduced pressure until a dry extract is obtained, which is purified by chromatography on silica eluting with a CH2Cl2/MeOH mixture 96/4 to afford 4.76 g of the expected product.

Workup

  1. extractionby extracting
  2. customdecanting
  3. washwashing
  4. extractionthen re-extracting with dichloromethane
  5. customThe organic phases are dried
  6. customevaporated under reduced pressure until a dry
  7. extractionextract
  8. customis obtained
  9. customwhich is purified by chromatography on silica eluting with a CH2Cl2/MeOH mixture 96/4

Sources & evidence

ORD record
ord-8333dba034514e338c6a62d1375b18fd
Source dataset
uspto-grants-2005_11
Patent number
US06960600B2

Reaction notes

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